ES2297371T3 - Derivados de polimeros de la guanidina como medicamento citostatico. - Google Patents
Derivados de polimeros de la guanidina como medicamento citostatico. Download PDFInfo
- Publication number
- ES2297371T3 ES2297371T3 ES04704150T ES04704150T ES2297371T3 ES 2297371 T3 ES2297371 T3 ES 2297371T3 ES 04704150 T ES04704150 T ES 04704150T ES 04704150 T ES04704150 T ES 04704150T ES 2297371 T3 ES2297371 T3 ES 2297371T3
- Authority
- ES
- Spain
- Prior art keywords
- guanidine
- cytostatic
- diamine
- molecular mass
- relative molecular
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229920000642 polymer Polymers 0.000 title claims description 6
- 229940126601 medicinal product Drugs 0.000 title 1
- 230000001085 cytostatic effect Effects 0.000 claims abstract description 22
- 239000000824 cytostatic agent Substances 0.000 claims abstract description 14
- 150000002357 guanidines Chemical class 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 4
- 150000004985 diamines Chemical class 0.000 claims description 12
- -1 polyoxypropylene Polymers 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 7
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 6
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 229920001515 polyalkylene glycol Polymers 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 16
- 206010028980 Neoplasm Diseases 0.000 description 9
- 201000011510 cancer Diseases 0.000 description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 8
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 210000004698 lymphocyte Anatomy 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 3
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 3
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 208000029742 colonic neoplasm Diseases 0.000 description 3
- 229960001904 epirubicin Drugs 0.000 description 3
- 229960002949 fluorouracil Drugs 0.000 description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 3
- 229960004857 mitomycin Drugs 0.000 description 3
- 201000002528 pancreatic cancer Diseases 0.000 description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000011275 oncology therapy Methods 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000007541 cellular toxicity Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009096 combination chemotherapy Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 231100000324 minimal toxicity Toxicity 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0017403A AT501983B1 (de) | 2003-02-04 | 2003-02-04 | Zytostatisches arzneimittel enthaltend ein polymeres guanidinderivat |
| ATA174/2003 | 2003-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2297371T3 true ES2297371T3 (es) | 2008-05-01 |
Family
ID=32831402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04704150T Expired - Lifetime ES2297371T3 (es) | 2003-02-04 | 2004-01-22 | Derivados de polimeros de la guanidina como medicamento citostatico. |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US7820719B2 (de) |
| EP (2) | EP1597302B1 (de) |
| JP (1) | JP4970929B2 (de) |
| KR (1) | KR20050109478A (de) |
| CN (1) | CN100339415C (de) |
| AT (2) | AT501983B1 (de) |
| AU (1) | AU2004208854B2 (de) |
| BR (1) | BRPI0407266A (de) |
| CA (1) | CA2515331A1 (de) |
| CY (1) | CY1107192T1 (de) |
| DE (2) | DE502004005602D1 (de) |
| DK (1) | DK1597302T3 (de) |
| EA (1) | EA011127B1 (de) |
| ES (1) | ES2297371T3 (de) |
| HK (1) | HK1088915A1 (de) |
| HR (1) | HRP20050697A2 (de) |
| IL (1) | IL170025A (de) |
| MX (1) | MXPA05008267A (de) |
| PT (1) | PT1597302E (de) |
| SI (1) | SI1597302T1 (de) |
| WO (1) | WO2004069898A1 (de) |
| ZA (1) | ZA200505991B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT501983B1 (de) * | 2003-02-04 | 2007-03-15 | Geopharma Produktionsgmbh | Zytostatisches arzneimittel enthaltend ein polymeres guanidinderivat |
| AT500998B1 (de) * | 2003-03-20 | 2008-10-15 | Geopharma Produktionsgmbh | Antimikrobiell wirkendes arzneimittel |
| WO2011008453A2 (en) | 2009-06-30 | 2011-01-20 | Monsanto Technology Llc | N-phosphonomethylglycine guanidine derivative salts |
| EP2338342A1 (de) | 2009-12-24 | 2011-06-29 | Sebastian Oberwalder | Polyharnstoff mit bioziden Eigenschaften |
| EP2338923B1 (de) | 2009-12-24 | 2017-10-18 | Sebastian Oberwalder | Polyurethan mit einem bioziden Polyharnstoff als Comonomer |
| AU2011322935A1 (en) | 2010-10-29 | 2013-05-30 | Mindinvest Holdings Ltd. | Liposomal drug composition containing a polymeric guanidine derivative |
| US20140228528A1 (en) * | 2011-11-02 | 2014-08-14 | Mindinvest Holdings Ltd. | Polyguanidine silicate and use thereof |
| AT513858B1 (de) * | 2013-01-25 | 2014-08-15 | Sealife Pharma Gmbh | Neue bioaktive Polymere |
| US20210299067A1 (en) * | 2018-06-21 | 2021-09-30 | Ucar Health Gmbh | Guanidinium derivatives as immunity-inducing agent |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2336605A (en) * | 1941-12-29 | 1943-12-14 | Du Pont | Pesticide |
| JPS5587145A (en) * | 1978-12-22 | 1980-07-01 | Fuji Photo Film Co Ltd | Developing method for silver halide photographic material |
| JPS59183698A (ja) | 1983-04-02 | 1984-10-18 | Wako Pure Chem Ind Ltd | 基質又は酵素活性の定量方法 |
| NL191481C (nl) | 1983-04-05 | 1995-08-04 | Draegerwerk Ag | Inrichting voor anesthesie met terugademing. |
| US4891423A (en) * | 1989-03-20 | 1990-01-02 | Stockel Richard F | Polymeric biguanides |
| DE4002404A1 (de) * | 1990-01-27 | 1991-08-01 | Degussa | Loesungen polymerer guanidinsalze mit erhoehter biozidwirksamkeit, verfahren zu ihrer herstellung und verwendung |
| DE4002403A1 (de) * | 1990-01-27 | 1991-08-01 | Degussa | Verfahren zur herstellung von biozid wirksamen polymeren guanidinsalzen |
| RU1816769C (ru) | 1990-12-28 | 1993-05-23 | Московский научно-исследовательский и проектно-изыскательский институт "МосводоканалНИИпроект" | Привитые сополимеры полиоксиалкилена на полиалкиленгуанидине в качестве поверхностно-активных веществ и катионного полиэлектролита |
| JP3716052B2 (ja) * | 1996-06-25 | 2005-11-16 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料の処理方法および脱銀処理組成物 |
| PT1280766E (pt) * | 2000-05-11 | 2005-05-31 | Poc Polymer Produktions Gmbh | Polimeros biocidas a base de sais de guanidina |
| AT501983B1 (de) * | 2003-02-04 | 2007-03-15 | Geopharma Produktionsgmbh | Zytostatisches arzneimittel enthaltend ein polymeres guanidinderivat |
-
2003
- 2003-02-04 AT AT0017403A patent/AT501983B1/de not_active IP Right Cessation
-
2004
- 2004-01-22 CN CNB2004800035490A patent/CN100339415C/zh not_active Expired - Fee Related
- 2004-01-22 DK DK04704150T patent/DK1597302T3/da active
- 2004-01-22 MX MXPA05008267A patent/MXPA05008267A/es active IP Right Grant
- 2004-01-22 EP EP04704150A patent/EP1597302B1/de not_active Expired - Lifetime
- 2004-01-22 SI SI200430596T patent/SI1597302T1/sl unknown
- 2004-01-22 BR BR0407266-9A patent/BRPI0407266A/pt not_active IP Right Cessation
- 2004-01-22 ES ES04704150T patent/ES2297371T3/es not_active Expired - Lifetime
- 2004-01-22 EA EA200501245A patent/EA011127B1/ru not_active IP Right Cessation
- 2004-01-22 ZA ZA200505991A patent/ZA200505991B/xx unknown
- 2004-01-22 AU AU2004208854A patent/AU2004208854B2/en not_active Ceased
- 2004-01-22 EP EP06020911A patent/EP1734064B1/de not_active Expired - Lifetime
- 2004-01-22 DE DE502004005602T patent/DE502004005602D1/de not_active Expired - Lifetime
- 2004-01-22 JP JP2006501334A patent/JP4970929B2/ja not_active Expired - Fee Related
- 2004-01-22 AT AT06020911T patent/ATE403690T1/de not_active IP Right Cessation
- 2004-01-22 PT PT04704150T patent/PT1597302E/pt unknown
- 2004-01-22 WO PCT/AT2004/000023 patent/WO2004069898A1/de active IP Right Grant
- 2004-01-22 KR KR1020057014225A patent/KR20050109478A/ko not_active Application Discontinuation
- 2004-01-22 CA CA002515331A patent/CA2515331A1/en not_active Abandoned
- 2004-01-22 DE DE502004007805T patent/DE502004007805D1/de not_active Expired - Lifetime
-
2005
- 2005-08-01 IL IL170025A patent/IL170025A/en not_active IP Right Cessation
- 2005-08-03 HR HR20050697A patent/HRP20050697A2/hr not_active Application Discontinuation
- 2005-08-03 US US11/197,465 patent/US7820719B2/en not_active Expired - Fee Related
-
2006
- 2006-08-22 HK HK06109319A patent/HK1088915A1/xx not_active IP Right Cessation
-
2008
- 2008-02-13 CY CY20081100168T patent/CY1107192T1/el unknown
-
2010
- 2010-09-27 US US12/891,181 patent/US8198333B2/en not_active Expired - Fee Related
-
2012
- 2012-06-12 US US13/494,812 patent/US20130040388A1/en not_active Abandoned
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